86023-29-2Relevant academic research and scientific papers
Versatile gold catalyzed transglycosidation at ambient temperature
Kayastha, Abhijeet K.,Hotha, Srinivas
experimental part, p. 7161 - 7163 (2012/07/31)
Glycosidation with stable alkyl glycosyl donors using a catalytic amount of gold salts is promising. Herein, 1-ethynylcyclohexanyl glycosides are identified as novel donors at room temperature and mechanistic investigation showed that the leaving group simply extrudes out.
13C NMR Spectroscopy, a Useful Tool To Determine the Enantiomeric Purity of Synthetic Threonine-Containing Glycopeptides. Spectra of Diastereoisomeric α- and β-D-Galactopyranosyl-L- and -D-threonine and -L- and -D-allothreonine
Pavia, A. A.,Lacombe, J. M.
, p. 2564 - 2568 (2007/10/02)
Further studies of O-glycosyl amino acids by natural-abundance 13C NMR spectroscopy are presented.Carbon-13 NMR spectra of diastereoisomeric α- and β-D-galactopyranosyl-L-threonine, -D-threonine, -L-allothreonine, and -D-allothreonine showed distinct anom
Un nouvel agent de glycosylation: l'anhydride trifluoromethanesulfonique. Synthese des α et β O-glycosyl-L-serine, -L-threonine et -L-hydroxyproline
Lacombe, J. M.,Pavia A. A.,Rocheville, J. M.
, p. 473 - 481 (2007/10/02)
When 2,3,4,6-tetra-O-benzyl-D-glucopyranose, -D-galactopyranose and 2,3,4-tri-O-benzyl-D-xylopyranose were allowed to react in the cold in dichloromethane or acetonitrile as solvent in the presence of trifluoromethanesulfonic (triflic) anhydride, with methyl or benzyl esters of the N-(benzyloxycarbonyl)-L-serine, -L-threonine, and -L-hydroxyproline, an anomeric mixture of the corresponding O-glycosylaminoacids was obtained (55 to 90percent overall yield), with the α-anomer being predominant.The same experimental procedure was successfully applied to the condensation of the benzyl ester of the N-(benzyloxycarbonyl)-L-hydroxyproline with 2,3,4-tri-O-benzyl-L-arabinopyranose and 2,3,5-tri-O-benzyl-L-arabinofuranose affording the corresponding condensation products with similar yield.Pure α and β anomers were obtained after column chromatography or crystallization with 30 to 65percent yield.Hydrogenolysis of benzyl derivatives afforded the unprotected compounds.Optical rotation, (1)H and (13)C nmr were the main methods used to assess structure and stereochemistry.
